Multi car conundrum

In our house, we have 4 licensed drivers.
Wife has a Kia Sportage (needs hitch for the yard waste trailer).
Daughter, Maria Andretti, has a good Vibe. (The double meanings both apply.)
Junior has what was my Mercury Grand Marquis. (It was a long term loan until he could afford a truck or inherit Grandpa's Sport Track. But he likes the big car a lot, even leaving the Masonic and Shrine stickers on the taillights.)
I have three "old" cars that I do not want to see salted roads.
1. My 91 5.0. The weather has not been kind to the rubber trim and MAACO paint job this last year.
2. My Covair that should finally be out of the restoration shop soon, and is ready for parades and local shows in addition to driving.
3. A 65 olds Cutlass Holiday coupe that's been in the family since ordered new.

Not that I drive every day or cannot take the Kia, but I no longer have a winter car. Insurance is telling me I have three toys, AKA “for pleasure use”.

I am considering selling the Olds, and have since I bought back the Corvair back (my first car). I've waited 23+ years to get the Olds repainted again. And before I started the LONG Corvair restoration, I swiped a road marker with the Cutlass. Finding the trim was difficult enouch to make me wonder about driving it. So a lot of the joy has been taken out of the car after replacing many parts at least twice over 34 years. Finding all the factory defects in the Holley carb was a drag, and there were many. Power disc brakes, paint and modern ratio power steering box would make it ready for regular driving and local shows, and parades. (The power drums have been rebuilt to new specs and are still not fun for highway panic stops!) But am I nuts for wanting to rehome it after 34 years in my name?
I could dig into tne Mustang, drive the Corvair when no salt is out, and have a simple, beater truck or another bandwagon Van for hauling stuff in if I sold the Cutlass. Or would I be selling a white elephant family member?
I'm not sure I am going to last long enough for two consecutive restorations that run long, although they would be paint and rubber parts projects. Oh, and brake upgrades. The interiors and drive trains are fine.
Maria wants the Cutlass in my will. Junior wants the 5.0. Neither drives a clutch yet, but that needs fixed anyway.

What are your thoughts and opinions?

Wow! I need to not type on my Kindle, especially after a long day! I edited the original post for readability.
If I do keep all three cars, I need to build a bigger detached garage. I still need a shop of some size anyway.

The car in question has not been driven in more than a year. I need to get the new insurance card in it and take it for a spin.
And as far as having the most toys, I have enough music stuff to be in the running. Those do need thinned out.

And as long as the bills are paid and I’m content, and she has something reliable to drive, the Mrs. does not care much what I do with the cars. Which is great. Except if I don’t like the result, it’s my fault only.

mustystang said:

If you have the space and can afford to keep them all, I would keep them. They are nice cars. Cars are meant to be driven though. Put bigger engines in them and make them fun to drive.

Make the 91 mustang the salt car. It's old and slow enough to see some abuse. I always put things in perspective of my 2008 v6, which I drive harddd. I definitely want something faster. That 91 gt may have more base hp and torque on paper, but over time those go down. Also use https://www.zeroto60times.com/vehicle-make/ford-0-60-mph-times/ to gauge. My 2008 v6, which I consider slow as molasses (pretty sure new v6 camry can smoke me), does 6.5 sec 0-60 mph and 15.3 sec qtr mile (using 2007 from website to estimate). 1991 GT, even with the extra base hp and torque, does 7.2 sec 0 to 60 and 15.6 sec qtr mile at best. Each year those numbers get slower due to degradation over time. Abuse that 91 gt like it was meant to be abused and have some fun. Do what you can to preserve it from the salt, but if it gets some salt it's not the end of the world. I'm drooling over the new gen mustangs and can't wait to have over 400 hp one day. The newer ones get better mpg too with more power, so it's a double win. Technology is cool.

Click to expand...

That’s been done.
I have time slips for the Mustang that calculate 325-350 Hp.
The Cutlass’ “high torque” 330 got slightly lowered compression, hardened valve seats and parts from Edelbrock to make up the difference.
The Corvair got a larger engine that also increased power while keeping it good for cruising.